Multi-step reaction with 13 steps
1.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h
2.1: potassium fluoride dihydrate; sodium bromide / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel
3.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 1.5 h / Inert atmosphere; Reflux
4.1: pyridine / dichloromethane / 3.33 h / 20 °C / Inert atmosphere
5.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 10 - 20 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: dipyridinium dichromate / dichloromethane / 18 h / 20 °C
8.1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / 2 h / Reflux
9.1: acetic anhydride / 16 h / 140 °C
10.1: trifluoroacetic acid / dichloromethane / 3 h / Cooling with ice
11.1: potassium carbonate; sodium iodide / ISOPROPYLAMIDE / 20 h / 53 °C / sealed tube
12.1: Oxone / methanol; water / 28.5 h / 0 - 50 °C
13.1: hydroxylamine / ethanol; water / 0.5 h / 140 °C / sealed tube; microwave
With
pyridine; dmap; Oxone; lithium aluminium tetrahydride; dipyridinium dichromate; potassium fluoride dihydrate; hydroxylamine hydrochloride; hydroxylamine; acetic anhydride; iron; sodium carbonate; potassium carbonate; ammonium chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium iodide; sodium bromide;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ISOPROPYLAMIDE; water; N,N-dimethyl-formamide; toluene;